Red azo dye.



and OTTO SIEBERT, of Berlin, in the Kingdom para-substituted meta-nitroamin or a para- -in order to convert the nitro group into an W'ILHELM HERZBERG AND OTTO PATENT OFFICE.

summer, or BERLIN, GERMANY, 7 ,AS{

SIGNORS TO AGTIEN GESELLSGHAFT FUR ANILIN FABRIKATION, OF

BERLIN, GERMANY.

5 RED AZO JDYE.

SPECIFICATION forming part of Letters Patent No. 704,826, dated July 15, 1 902.

Application filed March 3, 1902.

To all whom it may concern: I

Be it known that we, WILHELM HERZBERG of Prussia, German Empire, have invented new and useful Improvements in'Red Azo Dyerand we do hereby declare that the following is a full, clear, andexact description of the invention, which will enable others skilled in the art to which it appertains to makeand use the same. We have discovered that para-substituted meta amido alphyl sulfamido compounds represented by the typical formula:

(in which X means a substituted group; R and R, hydrogen atoms, which may be replaced by alkyl radicals) constitute most valuable components for the production of azo dyestuffs when combined with diazo compounds of nitro derivatives of ortho-amidophenol. The dyestuffs thus formed dye wool directly in an acid-bath bordeaux-red shades. If the dyed goods be subjected to a subsequent treatment with chromates or if dyeing be effected in thejwa'y described in theUnited- States Letters Patent No. 661,985, the shades become more bluish and get at the same time an extraordinary fastnessto soaping, milling,

pounds which we employ as starting products, .o they may be easily obtained by condensing a substituted mono-alkylated or a symmetric ally-dialkylated meta-diainin of the benzene series with an aromatic sult'ochlorid. In the first case a subsequent reduction is necessary amide group. For instance, the ortho-amido- Serial No 96,441. (specimens) para-toluol-para-sulfamido-toluol represented by the-typical formula:

tier/1-0m is prepared as follows: 15.2 parts of ortho- 6 nitro-para-amidmtoluol are suspended in one hundred and fifty parts of water, and while stirring well and heating the mixture on the water-bath twenty parts of para-toluolsulfochlorid are added thereto. In order to com- 'plete the reaction, six parts of sodium carbonate are graduallyadded. The condensationproduct thus formed may be directly filtered off. It is purified by re-solution in 111- luted alkali lye and repreoipitation by means of hydrochloric acid. 7 It melts at 164 centi-v grade. In order to transform this nitro compound into the corresponding amido c0m= pound, it is subjected to, the action of zinc= dust and hydrochloric acid or any other appropriate reducing agent.

The new product dissolves easily in diluted alkalies as well as in diluted mineral acids. From the solutions thus obtained it maybe precipitated by the addition of acetic acid or sodium acetate, respectively. It formsawhite crystallic powder melting at 160 Centigrade.

The following example, in which the parts are by weight, may serve to illustrate the preparation of our new dyestufis.

EwctmpZe-ilfaamfuciures of an (r20 dyestufi from picmmt'c acid and oriho-amt'do-para-toluoi-pa'ra-sulfcmido-toluol.-27.3 parts of ortho amide -para-toluol-para-sulfamidotoluol are dissolved in five hundred parts of water on addition of four parts of causticlsoda, and eleven parts of sodium carbonate are added thereto. To the solution obtained the diazo compound prepared in the well-known way from 21.4 parts of picramic acid is slowly run stufi, which is a sodium salt of an acid, havwhile coolingand stirring well. The new dyeing the formula separates directly. ltis filtered,pressed, and

dried. It forms in the dry state a reddishbrown powder which dissolves in water to an orange-red solution. The aqueous solution turns more yellowish on addition of causticsoda lye and separates a red precipitate on the addition of a mineral acid. It dissolves easily in concentrated sulfuric acid, forming a yellow solution. The alcoholic solution is red-colored. The new dyestulf produces on wool with the aid of chromium mordants intense bordeaux-red shades remarkable for (their fastness to soaping and milling and to the action of light and sulfurous acid.

The result is not materially changed if for the picramic acid para-nitro-ortho-amidophenol is substituted or if the ortho-amidopara-toluol-para-sulfamido-toluol is replaced by another para-substituted meta-amido-alphyl-sulfamid.

Having now described our invention and in what manner the same is to be performed, what we claim as new is' 1. The herein-described new azo dyestufis which are sodium salts of acids having the formula:

1 OH 1 CH, cm, 2 N=N c,H, 2) NH 4 N0 4 Nil-so, c nt-0H,

5 (in which Y means a hydrogen atom, which may be replaced by a nitro group, X a substituting group, and R and R hydrogen atoms which may be replaced by alkyl radicals) and which are obtained by combining 40 the diazo compound of a nitro derivative of ortho-amidophenol with a para-substituted meta-amido-alph yl-sulfamid; said dyestuffs forming in the dry state reddish-brown powders, soluble in water 'to orange-red solutions; the aqueous solutions turning somewhat more yellowish on addition of caustic-soda lye and separating red precipitates on the addition of mineral acids; the dyestufis dissolving readily in concentrated sulfuric acid to yellow solutions and in alcohol to red solutions; the dyes producing on wool with theaid of chromium mordants bordeauX-red shades of great intensity and fastness.

2. The herein-described new dyestufi'f which is a sodium salt of an acid having the formula: 5 5

1 OH 1 CH3 061g 2 N=NOGH2 2 NH,

(4 No, 4 NH-SO -g H-1 CH:;

lowsolution; dissolving in alcohol to a red solution; the dye producing on wool with the aid of chromium mordants intense bordeauxred shades of great intensity and fastness.

In witness whereof we have hereunto signed our names, this 15th day of February, 1902, in the presence of two subscribing witnesses.

- WILHELM HERZBERG.

OTTO SIEBERT.

WVitnesses HENRY HASPER, W OLDEMAR HAUPT. 

